More Lessons with Kelli Ch. 03

Writers Note: Things just keep getting better and better so enjoy because there is a lot more to come or cum as the saying goes.

I was really looking forward to our next visit with Jenna and Tim. It was a very busy month with closing my old store and moving to the new one, which was going to be the final break with me living as a man, so any chance for some playtime was welcome. Jenna told Ann that we had all played together and Ann was pissed that she missed being there to watch me get my ass reamed as she put it. But Jenna didn't say anything to her about Tim's interest in wearing women's clothing. Tim and Jenna each had two jobs and their schedules were pretty full but she talked to Jenna the next Sunday and told me that it worked out that they both had Wednesday night and Thursday morning free. I said that I would love to have them visit again, but Kelli said that there was one little catch and it was that neither Tim nor me could have sex from Monday until Wednesday night.

Kelli said, "This is Jenna's idea. She knows that he will be extra horny and it should be pretty hot when you two get together."

Which I to agreed since a couple of days usually didn't bother me much but by Wednesday, I was getting regular erections under my panties as I thought about the night to come. Before they got there I put on a sheer black bra and panties, black garter belt and stockings, and topped it all off with a dark blue satin blouse and a tight black skirt. I thought about putting on a slip and I have a really sexy black one but I had my own plans for the evening and decided that it wasn't necessary. Kelli did my hair and makeup, and prior to getting dressed I painted my fingernails and toenails dark red. She went with a cream colored dress but other than the sheer stockings, had on lavender colored lingerie. With our dresses on, we looked very sophisticated and once they came off, we both looked very sexy.

They showed up at seven-thirty and to our surprise, Tim was dressed as a woman. He had on a light blue knit dress that was short and very tight, with buttons all the way down the front. I was sure that he was wearing pantyhose under it, but I could see a panty line as well. He had a bra on but it wasn't filled with anything. Jenna had found the dress at a thrift store and did a great job with his hair and makeup. He had gotten his other ear pieced and was wearing a pair of Jenna's long hoop earrings.

I said, "Wow, aren't we the picture of loveliness tonight. You look really great."

Tim pointed to Jenna and replied, "It was her idea."

Jenna answered, "It wasn't that bad now was it?"

He said, "No, but I was scared that somebody would see me, especially when we stopped for gas right down the street from the apartment and she had me put it in!" Then he added, "Both of you also look really hot tonight."

I replied, "Thank you, but if you like the wrapping, wait until you see the present."

We all laughed and headed off to the kitchen so that we could finish getting supper ready. Tim said that Jenna wanted him to go out on Friday night dressed as woman but he was really unsure about it.

I said, "The more you do it, the easier it gets and I'm sure that Jenna has a place in mind that she knows will be safe for you."

He replied, "That is what she said."

I answered, "Trust me, I was really nervous my first time out."

Jenna who had been our waitress at the restaurant that first night said, "Elaine looked like she was expecting somebody to walk up behind her and yell, hey everybody, this is a man!"

After a long laugh I said, "It got easier after that and well look at me now. But the worst thing was that first trip to the ladies room."

Tim looked at Jenna and answered, "I hadn't even thought about that."

She smiled and shrugged her shoulders as I replied, "The trick is that you have to be totally cool. Go in, do your business sitting down, wipe afterwards, wash your hands, and get out.

Tim asked, "Wipe?"

I answered, "The tip of your dick. Besides, you don't want piss stains on your panties and if there is someone else in one of the stalls and they don't hear you getting some toilet paper, it could be a giveaway," and the girls laughed hard.

He said, "I think I should be writing all of this down."

"Just make it a habit whenever you are in panties, either at home or out on a date." I replied and said, "Get in and out of there as fast as possible and never check anyone out. Believe me, you will see the strangest shit in those places."

Jenna laughed hard because she had heard this story before and said, "Wait till you hear this, this is great!"

I said, "A couple of months ago we went to this hotel for supper and dancing at the club there and about the middle of the evening we went to the ladies room. We got out of the stalls, went to the sinks to wash our hands and standing down at the end, there was this younger looking gal. She was a little chubby and had huge boobs and for some reason she had her top off and was trying on bras in front of the mirror. I snuck a quick look in the mirror at her and the next thing I know, she says, hey lady, what do you think of this one? I turned, looked at it and said that I thought it was very lovely. I started to walk away and she says wait, takes that one off right in front of me, puts another one on and says, what about this one? I said that it was lovely too. Kelli grabbed my arm, pulled me out of there, and we weren't ten feet out of the door when we both started laughing and I don't think we stopped for five minutes."

Kelli smiled as she said, "'The best part was a little later that night she came over and danced with us for a couple of songs!"

Tim was laughing as he replied, "I really don't know what I would have done."

I told him about a few more things that I had seen. Like the one gal who had her mini-skirt pulled up and spent some time adjusting her thong in the mirror, and this older lady, who while she was bent close to the mirror checking her teeth, let loose with a fart so loud that it echoed off the bathroom walls.

After the laughter settled down, Kelli asked Jenna, "You did tell him about keeping a few Tampax in his purse just in case somebody asks him for one?"

Tim's face got red and he said, "Oh my god."

I laughed and answered, "Been there!"

We talked some about what kinds of things that Tim could do to be passable and comfortable, all of which I had learned from Kelli. Jenna and Kelli had gone different directions as far as their persona as would be.

Jenna said, "I just wanted to be that hot chick waitress at the bar that everybody looks at and they do. I know I will have to grow up some day, settle down, get married, and pop out a half dozen kids or so," and again the laughter was loud and long.

Kelli on the other hand never wanted to be flashy or for that matter even noticed, except when it mattered. She had watched lots of old movies and modeled herself, not off of any one actress, but a collage of how they talked and walked and even dressed. She had found a stack of women's fashion magazines from the 1960's in a used bookstore, and had studied them over and over.

She said, "My older sister is a bit more sensible but Ann was always doing something wild with her clothes and I just didn't want that for myself. I am not knocking you Jenna because you are good at what you do and you are having fun. But I am happy with how I am and well," after smiling at me, finished with, "I am doing pretty good myself."

All in all it was a good talk and a lot of fun. Once in a while Tim and I would look at each other for a few seconds with that look that pretty much means one thing.

Jenna caught us doing it the one time and said, "Look at these two with the eye action. If I didn't know any better I would think that they are up to something."

I replied in a real sexy voice, "The only thing she had better be up to later is deep inside of me!"

Tim blushed again and everybody started laughing hard. A little later he asked how Kelli and I met, so we told him about her coming to me for guitar lessons and how things progressed after that. He said that he had played guitar and bass in a few bands, so after supper, I took Tim down to the basement. Before I met Kelli I had a small recording setup at my store for my own use which I had since moved to Kelli's house. We talked about music and that kind of stuff for a while, and I played him a couple of tracks that I had recorded.

As I got up from my chair, I saw that Tim was looking at me and as I walked over he said, "If I would really stop and think about it, this is so crazy."

I smiled and replied, "I gave up thinking that way soon after I met Kelli. Now it's more important to enjoy life and love and so what if I do it dressed as a woman?"

"I guess," Tim answered, "And even from the first time that I went to bed with Jenna knowing that she had been a man, it just felt right."

"I will tell you something, I don't live with Jenna and know her day to day, but after hearing about some of the relationships that she has been in, I really think that if you give it your all, she is going to do the same back and a lot more," I answered and added, "The rest, it was pretty intense the last time you guys were here but it was also a lot of fun and if you don't like getting dressed up as a woman, just tell her that."

He laughed and replied, "No, I am starting to really like this, although that is scaring me a little and I really like being with you and Kelli. I was nervous, but like being with Jenna, it felt so natural."

"That it does," I said as I moved close and gently kissed him. He hugged me tightly and started getting more passionate, but I stopped him and said, "Go easy. Kiss me like you are a woman kissing me for the first time."

Tim replied, "Okay," and we resumed the kiss and it was gentle but very nice. He put his cheek next to mine, and said, "I have to tell you, my balls feel like they are going to explode. It used to be that I would go a couple of weeks without sex with no problems but since I met Jenna, I am horny all the damn time."

I answered, "Just think how good it going to feel."

With a laugh he said, "If I think too much about, I'm going to cum in my panties," and I laughed as well.

I replied, "Do you know what I do? I don't think about having a cock or balls until I need them."

He looked at me for a while and said, "I never thought about doing that but anytime I put on panties I always get a hard-on."

I answered, "That goes away after a while."

We kissed again very gently and went back upstairs. The girls were sitting close together at one end of the couch talking, so Tim and I sat at the other end.

Jenna said, "I think tonight is going to be very hot."

I replied, "We were discussing that."

Jenna answered, "I figured that you were."

Kelli said, "I think it is time that Tim had a proper name."

He replied, "Yeah, we have talked about that a little. I just don't know what to call myself."

I answered, "Just pick something simple that you would be comfortable telling someone else what it is. That is why I picked Elaine, it fits well with me being older and it is classy."

He thought for a little while, looked over at Jenna a couple of times, then once at me, before saying, "I like Beth."

Kelli replied, "I really think that name suits you and when you want to be a little more formal, there is Elizabeth."

Jenna added, "I think it is great."

He laughed and said, "Now all I need are boobs!"

I replied, "I have pair of D size ones upstairs that you are more than welcome to."

He looked at my breasts, then measured with his hands on how far out they would stick, before saying, "Thanks but they might be a little big."

I answered, "They are silicone and with some careful trimming you could get them down to whatever size you want."

"Worth a try," he replied.

Kelli went and mixed us a round of drinks and the conversation was light and fun. Tim, now Beth, and I made out a little as we talked and the girls were doing the same.

Around nine-thirty, I looked over at Kelli and she nodded her head yes, so I said, "I think it is time." We all headed upstairs and when we got to the top I said, "I would like to do something different tonight."

Jenna asked, "What?"

I answered, "I think that nightgowns would be nice, but why don't we undress each other first."

Kelli answered, "That sounds like fun."

Jenna went over to the other bedroom to get a couple for them and Kelli got a couple of our long ones out of the closet. I lit the candles, turned out the lights, and got some slow jazz playing on the stereo.

Jenna came back with their nightgowns and said, "I see that you got a new bed. I'm surprised that you didn't get one of those nice big round ones."

Kelli and I laughed, and Kelli replied, "I will tell you all about that later.

Jenna answered, "Okay," as she set the nightgowns on the end of the bed and got close to Kelli.

I moved tightly against Beth and we started dancing. We kissed and touched, then kissed some more. I made the first move as I unbuttoned the top of her dress and Beth did the same with my blouse. I figured that the girls were doing the same but I wasn't really watching them. Soon my blouse was completely opened and her dress was unbuttoned down to her waist, then she opened the cuffs on my blouse and slid it off of me.

I whispered, "Just drop it," which she did.

I pushed her dress off of her shoulders and our bras touched as we kissed again. I felt her hands at the clasp of mine and I did the same with her bra and we just let them drop. Our breasts touched and Beth let out a soft moan of passion. She felt around until she found the button at the back of my skirt, which she opened along with the zipper and carefully, pushed it down over my hips. I finished removing her dress and Beth played with my ass for a while. Under her pantyhose she had on pink boy short panties and there was a noticeable wet spot from her precum but by then, I had one on my panties as well. I gently rolled down the top of the pantyhose and helped her get out of those and she undid my garters and slowly pushed my stockings down my legs. We stroked each other's cock through the panties, then my garter belt and both of our panties hit the floor. We got close and as our bare cocks touched, she let out another low moan. We danced and kissed for a while then I went to get our nightgowns and Kelli was at the bed getting their gowns.

We kissed and she whispered, "That was so beautiful and very hot."

After another kiss again I returned to where Beth was standing. I put the sheer purple nightgown on her and handed her mine, which was ivory in color with lace cups that clearly showed off my breasts, and we resumed our dancing and kissing.

After a couple of minutes I softly said, "Make love to me Beth."

She took my hand and led me to the bed and the girls moved over there at the same time. We got in and resumed our kissing and foreplay. After spending lots of time on my breasts with her hands and mouth, she slid her hand down until it came to rest on my cock, but I pulled it away and shook my head no.

Beth looked at me with a puzzled look and I said, "Forget that it is there. Right now I am a woman."

She smiled and this time she reached down, moved my nightgown up and traced her finger down the side of my leg and into my crack until she touched my asshole. She lightly rubbed around it and pushed against it a couple of times, before she reached back and got the lube and some tissues. I watched as she put a little on her middle finger, which she returned to my ass. After rubbing it around the outer edges, Beth put some more on her finger, set the lube down and I felt her finger once again, but this time she slowly pushed it in. I brought my legs up a little, we kissed as she fingered my ass and I closed my eyes as I savored the sensation.

A minute passed and I heard Jenna say, "That is so damn hot that if I still my cock, I would have cum twice just watching you girls."

The sound of laughter went though the room and after a little more fingering, Beth softly said, "It is time."

I watched as she got between my legs and lubed her cock and in the dim light the head looked even larger than the first time. As she got close, I pulled my legs back, and felt it against my ass. I closed my eyes as she slowly pushed in and it did feel bigger but this time it felt so good going in. I opened my eyes and she put her arms under my legs and I placed mine on her back. She moved very slowly with long strokes that traveled the distance of my ass and I could tell that she was fighting the urge to cum. The room was quiet except for the sounds of the girls making love, they had switched to a sixty-nine with Kelli on top, but I could see them glancing over and watching us. I heard Jenna climax and then Kelli, but I was too lost in what I was feeling and as more time went by, Beth was really fighting to hold back.

I pulled her down, kissed her and said, "Fill me."

She pulled her cock about halfway out, pumped faster, and pushed in deep just as she started to cum. I felt the throb and my insides were flooded with her sperm and my breaths kept pace with her cock as each stroke released more inside of me. If Beth had gone on much longer I might have climaxed myself it felt that good. She went back to long slow strokes, and we kissed until her cock went down. Our eyes locked on each other and the look in her eyes was every bit as intense as the one that I had in mine.

I looked over at the girls who had gotten quiet as he moved off of me, and headed to the bathroom and said, "You wanted hot, right?"

Kelli moved off of Jenna, crawled over to me and kissed me long and deep before saying, "That was unbelievable."

With a smile I replied, "You should have seen it from where I was sitting," and we laughed.

Jenna shook her head a few times and then walked into the bathroom while Beth was still in there. There was a puddle of sperm collecting under my ass, so Kelli got some tissues, wiped up the bed and then my ass, before taking a clean one and putting it against my asshole.

With a laugh and that wild look in her eyes she asked, "Should I get you a Tampax?"

I laughed as well, but I didn't answer, then we kissed some more as Jenna and Beth came out of the bathroom smiling and laughing. I decided to go wash up a little and Kelli went with me.

We kissed and she said, "You really got into that, didn't you?"

I replied, "It was pretty intense, but I still love you and only you."

Kelli answered, "And I still love you and only you," and after another kiss we were back out in the bedroom.

Beth was waiting for me on the same side of the bed where she had made love to me and the foreplay was pretty much a repeat of what she had done to me. I didn't touch her cock or balls, well, not intentionally, but I stroked the insides of her thighs and played with her ass cheeks from between her legs. I took a lot of time as I lubed her with one finger, before adding a second one and the kissing between us was almost nonstop. The girls had resumed their play and I knew that they were watching the show. After I finished with that, I wiped my fingers on a tissue and Beth started to get on her knees, but I gently pushed her on her back. She pulled her nightgown up a little before lifting her legs as I was lubing my cock, but I moved it back down to cover her already hard cock as I got between her legs. We looked at each for a few seconds and I slowly entered her.

Beth had been holding her breath as I did, then after letting it out slowly said, "Oh yes."

Between not having done for a few days, plus getting worked up as Beth's cock worked it's magic inside my ass, my cock was already feeling like it was ready to explode. I went slowly at first until I got things under control. Then I started going a little faster, and after a little while I started to rotate my hips a little as I went in and Beth's eyes got very wide.